First Aldol Cross-Linked Hyaluronic Acid Hydrogel: Fast and Hydrolytically Stable Hydrogel with Tissue Adhesive Properties

Daniel Bermejo-Velasco, Sandeep Kadekar, Marcus Vinicius Tavares Da Costa, Oommen P. Oommen, Kristofer Gamstedt, Jöns Hilborn, Oommen P. Varghese

    Research output: Contribution to journalArticleScientificpeer-review

    39 Citations (Scopus)

    Abstract

    Currently, there are limited approaches to tailor 3D scaffolds cross-linked with a stable covalent C-C bond that does not require any catalysts or initiators. We present here the first hydrogels employing aldol condensation chemistry that exhibit exceptional physicochemical properties. We investigated the aldol-cross-linking chemistry using two types of aldehyde-modified hyaluronic acid (HA) derivatives, namely, an enolizable HA-aldehyde (HA-Eal) and a non-enolizable HA-aldehyde (HA-Nal). Hydrogels formed using HA-Eal demonstrate inferior cross-linking efficiency (due to intramolecular loop formation), when compared with hydrogels formed by mixing HA-Eal and HA-NaI leading to a cross-aldol product. The change in mechanical properties as a result of cross-linking at different pH values is determined using rheological measurements and is interpreted in terms of molecular weight between cross-links (Mc). The novel HA cross-aldol hydrogel demonstrate excellent hydrolytic stability and favorable mechanical properties but allow hyaluronidase-mediated enzymatic degradation. Interestingly, residual aldehyde functionality within the aldol product rendered the tissue-adhesive properties by bonding two bone tissues. The aldehyde functionality also facilitated facile post-synthetic modifications with nucleophilic reagents. Finally, we demonstrate that the novel hydrogel is biocompatible with encapsulated stem cells that show a linear rate of expansion in our 3-6 days of study.

    Original languageEnglish
    Pages (from-to)38232-38239
    JournalACS Applied Materials and Interfaces
    Volume11
    Issue number41
    Early online date2019
    DOIs
    Publication statusPublished - Oct 2019
    Publication typeA1 Journal article-refereed

    Keywords

    • aldol chemistry
    • biomaterial
    • hyaluronic acid
    • hydrogel
    • tissue adhesive

    Publication forum classification

    • Publication forum level 2

    ASJC Scopus subject areas

    • General Materials Science

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